I Joined Airbnb at 52, and Here’s What I Learned About Age, Wisdom, and the Tech Industry

A growing number of people feel like an old carton of milk, with an expiration date stamped on their wrinkled foreheads. One paradox of our time is that Baby Boomers enjoy better health than ever, remain young and stay in the workplace longer, but feel less and less relevant. They worry, justifiably, that bosses or potential employers may see their age more as liability than asset. Especially in the tech industry.

And yet we workers “of a certain age” are less like a carton of milk and more like a bottle of fine wine — especially now, in the digital era. The tech sector, which has become as famous for toxic company cultures as for innovation, and as well-known for human resource headaches as for hoodie-wearing CEOs, could use a little of the mellowness and wisdom that comes with age.

I started a boutique hotel company when I was 26 and, after 24 years as CEO, sold it at the bottom of the Great Recession, not knowing what was next. That’s when Airbnb came calling. In early 2013 cofounder and CEO Brian Chesky approached me after reading my book Peak: How Great Companies Get Their Mojo from Maslow. He and his two Millennial cofounders wanted me to help turn their growing tech startup into an international giant, as their Head of Global Hospitality and Strategy. Sounded good. But I was an “old-school” hotel guy and had never used Airbnb. I didn’t even have the Uber app on my phone. I was 52 years old, I’d never worked in a tech company, I didn’t code, I was twice the age of the average Airbnb employee, and, after running my own company for well over two decades, I’d be reporting to a smart guy 21 years my junior. I was a little intimidated. But I took the job.

On my first day I heard an existential tech question in a meeting and didn’t know how to answer it: “If you shipped a feature and no one used it, did it really ship?” Bewildered, I realized I was in deep “ship,” as I didn’t even know what it meant to ship product. Brian had asked me to be his mentor, but I also felt like an intern.